WO2014064716A1 - Dérivés de (5h)-1-benzopyran-5-one et formulations destinés à des applications de parfumerie et aromatiques - Google Patents

Dérivés de (5h)-1-benzopyran-5-one et formulations destinés à des applications de parfumerie et aromatiques Download PDF

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Publication number
WO2014064716A1
WO2014064716A1 PCT/IN2013/000645 IN2013000645W WO2014064716A1 WO 2014064716 A1 WO2014064716 A1 WO 2014064716A1 IN 2013000645 W IN2013000645 W IN 2013000645W WO 2014064716 A1 WO2014064716 A1 WO 2014064716A1
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WO
WIPO (PCT)
Prior art keywords
mol
general formula
benzopyran
compound
hexahydro
Prior art date
Application number
PCT/IN2013/000645
Other languages
English (en)
Inventor
Sujata BHAT
Sylvia FERNANDES
Kedar VAZE
Original Assignee
S. H. Kelkar & Company Pvt. Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by S. H. Kelkar & Company Pvt. Ltd. filed Critical S. H. Kelkar & Company Pvt. Ltd.
Publication of WO2014064716A1 publication Critical patent/WO2014064716A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms

Definitions

  • ADDRESS Lai Bahadur Shastri Marg, Mulund West, Mumbai 400 080,
  • the present invention generally relates to synthesis of a class of compounds, having musky odor with fruity, aromatic, saffron like notes reminiscent of cashmeran®. More particularly, the present invention pertains to the odorants consisting of substituted hexahydro-(5H)- 1 -benzopyran-5 -one and tetrahydro-(SH)- 1 -benzopyran-5-one derivatives and methods of synthesis and perfumery/flavor/cosmetic applications thereof.
  • odorants are presently utilized in the perfumery industry. Typically, these odorants are synthetic molecules based on naturally occurring fragrances. A particularly desirous and well known fragrance is "Musk”. In nature, several different aromas contribute to the overall Musk fragrance profile. As such, it is difficult to achieve a single molecule that is an acceptable synthetic replacement.
  • An embodiment of the present invention pertains to molecules of general formula A namely substituted hexahydro-(5H)-l-benzopyran-5-one derivatives wherein each of R], R 2 , R 3 , R4, R 5 , R6, R 7 , R 8 , R 9 and R )0 are independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl or similar groups.
  • Yet another embodiment of the present invention relates to the odorant molecules of formula B namely substituted tetrahydro-(5H)-l-benzopyran-5-one derivatives, wherein each of Ri, R 2 , R3, 4, R5, 3 ⁇ 4, R7, Rs and R 9 are independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl or similar groups.
  • Yet another embodiment of the present invention pertains to an odorant including the compound of general formula A. Yet another embodiment of the present invention relates to a fragrance including the compound of general formula B.
  • Yet another embodiment of the present invention pertains to a perfumery composition comprising an olfactory acceptable amount of the compound of general formula A.
  • Yet another embodiment of the present invention pertains to a perfumery composition comprising an olfactory acceptable amount of the compound of general formula B.
  • Yet another embodiment of the present invention pertains to a method of synthesizing the compound of general formula A.
  • compounds of formula A are synthesized by reacting cyclohexadione by using in situ condensation reactions with aldehyde or ketone (or the corresponding dialkyl acetals, ketals) and vinyl ether in the presence of mild basic condition.
  • Yet another embodiment of the present invention pertains to a method of synthesizing the compound of general formula A.
  • compounds of general formula A are synthesized by reacting cyclohexadione by using in situ condensation reactions with aldehyde or ketone and alkene in the presence of mild basic condition.
  • Yet another embodiment of the present invention pertains to a method of synthesizing the compound of general formula B. In this method, compounds of general formula B are synthesized from compounds of general formula A by using elimination reaction in the presence of acidic condition.
  • Yet another embodiment of the present invention pertains to a method of synthesizing the compound of general formula B.
  • compounds of general formula B are synthesized from substituted cyclohexadione by using condensation and elimination reaction in the presence of mild basic followed by acidic catalysts.
  • Embodiments of the invention provide a novel odorant, namely and variations thereof, methods of synthesis, and perfumery compositions thereof.
  • the novel odorant includes a compound of general formula A:
  • each of Ri, R 2 , R3, R4, R5, Re, R7, R 8 , R9 and R ]0 are independently selected from the group consisting of hydrogen, methyl, ethyl , w-propyl, isopropyl, w-butyl, isobutyl, «-pentyl, isopentyl or similar groups.
  • inventions of the invention provide a novel odorant molecule, namely substituted tetrahydro-(5H)-l-benzopyran-5-one derivatives of general formula B and variations thereof and methods of synthesis thereof.
  • the novel odorant contains a compound of general formula B.
  • each of Rj, R 2 , R3, R4, R5, 3 ⁇ 4, R7, Rs and R 9 are independently selected from the group consisting of hydrogen, methyl, ethyl , rc-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl or similar groups.
  • the compounds exhibit a Musky aroma with fruity, aromatic, saffron like notes reminiscent of cashmeran® that is similar or identical to the natural Musk aroma.
  • perfumery compositions having the novel compound described herein may exhibit a woody aroma that is similar or identical to the natural Musk aroma.
  • this increased stability results in a corresponding increase in persistence of the aroma given off by the perfumery compositions and therefore facilitates perfumery compositions having a decreased concentration of the odorant that provides a longer lasting aroma as compared to conventional perfumery compositions.
  • Suitable perfumery compositions generally include a perfume, a cologne, an eau du toilette, an eau du perfume, a cosmetic, a personal care compound, a cleansing compound, a fabric softener, an air freshener, and the like. Furthermore, it is within the purview of embodiments of the invention that the novel compounds described herein may be integrated into building materials, wall and floor coverings, vehicle components, and the like. In general, in addition to the novel odorant described herein, suitable perfumery compositions include conventional ingredients such as, for example, solvents, carriers, stabilizers, emulsifiers, moisturizers, dispersants, diluents, thickeners, thinners, other odorants, adjuvants, and the like.
  • novel compound of general formula A and B may be synthesized according to the following Schemes 1-3 in which each of Ri, R 2 , R3, R4, R5, R6, R7, Rs, R9 and Rio are independently selected from the group consisting of hydrogen, methyl, ethyl, H-propyl, isopropyl, w-butyl, isobutyl, rc-pentyl, isopentyl or similar groups.
  • hexahydro-(5H)-l-benzopyran-5-one and tetrahydro-(5H)- l-benzopyran-5-one derivatives are synthesized in a variety of methods starting with the reactants cyclohexadione or substituted cyclohexadione, a carbonyl compound and a vinyl ether.
  • hexahydro- (5H)-l-benzopyran-5-one and tetrahydro-(5H)-l-benzopyran-5-one derivatives and variations thereof may be synthesized in any suitable manner.
  • SCHEME 1 Synthesis of hexahydro-(5H)-l-benzopyran-5-one derivatives
  • EXAMPLE 3 Synthesis of 4,4-dimethyl-2-ethoxy-2 ⁇ ,4,6,7,8-hexahydro-(5H)-l- benzopyran-5-one, [4,4-dimethyl-2-ethoxy-2,3,4,6,7,8-hexahydro-(5H)-chromen-5- one] A 3 ⁇ 4
  • EXAMPLE 6 Synthesis of 2-ethoxy-4-ethyl-2,3,4,6,7,8-hexahydro-(5H)-l- benzopyran-5-one, [2-ethoxy-4-ethyl-2 ⁇ ,4,6,7,8-hexahy dro-(5H)-chromen-5-one] ,
  • EXAMPLE 15 Synthesis of 2-ethoxy-2,3,4,6,7,8-hexahydro-4- i-butyl-(5H)-l- benzopyran-5-one, [2-ethoxy-2-3,4,6,7,8-hexahydro-4-/i-butyl-(5H)-chromen-5- one], As
  • EXAMPLE 17 Synthesis of 2-ethoxy-2 ⁇ A6/7,8-hexahydro-4-isopropyl-(5H)-l- benzopyran-5-one, [2-ethoxy-2,3,4,6,7,8-hexahydro-4-isopropyl-(5H)-chromen-5- one], Ai
  • EXAMPLE 18 Synthesis of 7.7-dimethyl-2-ethoxy-4-isopropyl-2,3,4,6,7,8- hexahydro- (5H)-l-benzopyran-5-one, (7,7-dimethyl-2-ethoxy-4-isopropyl- 2,3,4,6,7,8-hexahydro-(5H)-chromen-5-one), Aio
  • perfumery composition having a Musky character, was prepared by mixing the following ingredients:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un mode de réalisation de la présente invention concerne des molécules de formule générale A et de formule générale B, à savoir des dérivés de hexahydro-(5H)-1-benzopyran-5-one (ou hexahydro-(5H)-chromen-5-one) substitués et des dérivés de tétrahydro-(5H)-1- benzopyran-5-one (ou tétrahydro-(5H)-chromen-5-one) substitués respectivement, chacun des R1, R2, R3, R4, R5, R6, R7, R8, R9 et R10 étant indépendamment sélectionnés dans le groupe comprenant hydrogène, méthyle, éthyle, n-propyle, isopropyle, n-butyle, isobutyle, n-pentyle, isopentyle ou des groupes similaires. Ce brevet comprend des procédés de synthèse de composés de la formule générale A et de composés de la formule générale B et des compositions de parfumerie/cosmétique comprenant une quantité acceptable d'un point de vue olfactif du composé de formule A et/ou B. L'invention concerne également une formulation de parfumerie contenant des composés de la formule générale A et/ou B.
PCT/IN2013/000645 2012-10-25 2013-10-21 Dérivés de (5h)-1-benzopyran-5-one et formulations destinés à des applications de parfumerie et aromatiques WO2014064716A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN3097/MUM/2012 2012-10-25
IN3097MU2012 2012-10-25

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WO2014064716A1 true WO2014064716A1 (fr) 2014-05-01

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022024054A1 (fr) 2020-07-31 2022-02-03 S H Kelkar And Company Limited Odorisants et compositions comprenant des odorisants
WO2024023169A1 (fr) * 2022-07-29 2024-02-01 Givaudan Sa Dérivés de chromène-5-one utilisés comme parfums

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BERGER S ET AL: "Ruthenium-catalyzed addition of carboxylic acids or cyclic 1,3-dicarbonyl compounds to propargyl alcohols", TETRAHEDRON LETTERS, PERGAMON, GB, vol. 51, no. 50, 15 December 2010 (2010-12-15), pages 6630 - 6634, XP027484126, ISSN: 0040-4039, [retrieved on 20101016], DOI: 10.1016/J.TETLET.2010.10.053 *
GANESH PANDEY, SAUMEN HAJRA, MANAS K. GHORAI, AND K. RAVI KUMAR: "Designing Photosystems for Harvesting Photons into Electrons by Sequential Electron-Transfer Processes: Reversing the Reactivity Profiles of alpha,beta-Unsaturated Ketones as Carbon Radical Precursor by One Electron Reductive beta-Activation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 119, no. 38, 24 September 1997 (1997-09-24), pages 8777 - 8787, XP002720519, DOI: 10.1021/ja9641564 *
HARAYAMA, TAKASHI; TAKATANI, MUNEO; INUBUSHI, YASUO: "The stereochemistry of Diels-Alder adduct of 2-(3-acetoxypropyl)-5-methylcyclohex-2-en-1-one with butadiene", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 27, no. 3, 1979, pages 726 - 730, XP002720521, DOI: 10.1248/cpb.27.726 *
LI LI, QI WU, BO-KAI LIU, XIAN-FU LIN: "Facile Multicomponent Synthesis of Novel 2,3-Dihydropyran Derivatives under Solvent-Free Conditions", SYNTHESIS, vol. 4, 21 January 2011 (2011-01-21), pages 563 - 570, XP002720520, DOI: 10.1055/s-0030-1258417 *
ROBERT M. COATES, STEVEN J. HOBBS: "alpha-Alkoxyallylation of activated carbonyl compounds. A novel variant of the Michael reaction", JOURNAL OF ORGANIC CHEMISTRY, vol. 49, no. 1, 1984, pages 140 - 152, XP002720518, DOI: 10.1021/jo00175a030 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022024054A1 (fr) 2020-07-31 2022-02-03 S H Kelkar And Company Limited Odorisants et compositions comprenant des odorisants
WO2024023169A1 (fr) * 2022-07-29 2024-02-01 Givaudan Sa Dérivés de chromène-5-one utilisés comme parfums

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